2-(((1R,2S)-2-hydroxy-1,2-diphenylethylimino)methyl)phenol | 548772-24-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(((1R,2S)-2-hydroxy-1,2-diphenylethylimino)methyl)phenol
• 英文别名: (1S,2R)-(OH)(C6H4)CHN(CHPh)2OH；(1R,2S)-2-((2-hydroxy-1,2-diphenyl-ethylimino)-methyl)-phenol；2-[[(1R,2S)-2-hydroxy-1,2-diphenylethyl]iminomethyl]phenol
• CAS: 548772-24-3
• 化学式: C₂₁H₁₉NO₂
• 分子量: 317.387
• InChiKey: BCYPKVNJMLMPFO-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(((1R,2S)-2-hydroxy-1,2-diphenylethylimino)methyl)phenol 、 苯硼酸 以 甲苯 为溶剂， 以63%的产率得到(4S,5R)-2-(phenyl)benzo[j]-4-phenyl-5-phenyl-6-aza-1,3-dioxa-2-boracyclononen-6-ene
  参考文献：
  名称：

  新型手性五六元环[4.3.0]单体硼酸盐杂环双环体系的合成，表征和X射线研究

  摘要：

  通过席夫碱和苯基硼酸的反应制备了九种新的硼酸盐，其中六种为手性，具有五六元环杂环。通过光谱技术，1 H，13 C，11 B NMR ，红外光谱，质谱和元素分析对硼酸盐进行了全面表征。该反应显示出高的非对映选择性，仅在化合物4c在脂族部分中包含甲基取代基的情况下，诱导很低，得到两种非对映异构体的2∶1混合物。结果表明，杂环中优选的立体化学是五元环中的所有取代基和与硼原子相连的苯基均在同一侧。

  DOI：

  10.1016/j.jorganchem.2011.03.006
• 作为产物：
  描述：

  (1S,2R)-2-氨基-1,2-二苯基乙醇 、 水杨醛 以 甲醇 为溶剂， 反应 8.0h， 生成 2-(((1R,2S)-2-hydroxy-1,2-diphenylethylimino)methyl)phenol
  参考文献：
  名称：

  A pair of Schiff base enantiomers studied by absorption, fluorescence, electronic and vibrational circular dichroism spectroscopies and density functional theory calculation

  摘要：

  一对对映异构体席夫碱被合成和表征，特别是它们的绝对构型通过振动圆二色性光谱确定。

  DOI：

  10.1039/c5ra02154e

文献信息

• X-Ray crystallographic and spectroscopic properties of eight Schiff bases as evidence of the proton transfer reaction. Role of the intermolecular hydrogen bond
  作者：Oscar Domínguez、Braulio Rodríguez-Molina、Mario Rodríguez、Armando Ariza、Norberto Farfán、Rosa Santillan

  DOI：10.1039/c0nj00179a

  日期：——

  corresponding crystal structures were analyzed in order to identify their characteristic hydrogen bonding patterns. The X-ray analysis showed that the enol (O–H⋯N) tautomer is the most stable in compounds 1–3 whereas the keto (N–H⋯O) form is preferred in compounds 4–7. The specific intermolecular O–H⋯O hydrogen bonding interactions that control the supramolecular arrangement of each tautomer are discussed.

  进行了几种邻羟基席夫碱的光谱研究，并分析了相应的晶体结构，以确定其特征性的氢键模式。X射线分析表明，烯醇（O–H⋯N）互变异构体在化合物1-3中最稳定，而酮基（N–H⋯O）形式在化合物4–7中更可取。讨论了控制每个互变异构体超分子排列的特定分子间O–H⋯O氢键相互作用。此外，使用固态NMR和IR实验可以对多晶样品进行完整的表征。还使用溶液VT NMR和紫外可见光实验获得有关互变异构体性质和稳定性的宝贵见解。
• Synthesis, characterization and X-ray studies of new six–seven membered rings [4.5.0] heterobicyclic system of monomeric boronates
  作者：José María Rivera、Enrique Méndez、Raúl Colorado-Peralta、Susana Rincón、Norberto Farfán、Rosa Santillán

  DOI：10.1016/j.ica.2012.03.055

  日期：2012.7

  Different tridentate ligands derived from ethanolamines and 2-hydroxyacetophenone, 2-hydroxybenzophenone and salicylaldehyde were reacted with two equivalents of phenylboronic acid to obtain compounds 6a-6f which are [4.5.0] heterobicyclic systems with a B-O-B structural unit. The boronates were fully characterized and two heterobicyclic [4.5.0] structures have been analyzed by X-ray crystallography, where a series of parameters such as bond distances, bond angles, torsion angles, tetrahedral character at the boron atom and deviation of the boron atom from the mean plane have been evaluated. (C) 2012 Elsevier B.V. All rights reserved.
• Enantioselective nitroaldol (Henry) reaction catalyzed by chiral Schiff-base ligands
  作者：Mehmet Çolak、Nadir Demirel

  DOI：10.1016/j.tetasy.2008.02.005

  日期：2008.3

  Chiral Schiff-bases 2, 3, 4 and 5 were designed for the enantioselective nitroaldol (Henry) reaction. The highest enantioselectivity was observed for ligand 4 (82% ee) when CH2Cl2 was used as a solvent. (C) 2008 Elsevier Ltd. All rights reserved.
• Titanium complexes of chiral amino alcohol derived Schiff bases as efficient catalysts in asymmetric oxidation of prochiral sulfides with hydrogen peroxide as an oxidant
  作者：Prasanta Kumar Bera、Debashis Ghosh、Sayed Hasan Razi Abdi、Noor-ul Hasan Khan、Rukhsana Ilays Kureshy、Hari Chandra Bajaj

  DOI：10.1016/j.molcata.2012.04.014

  日期：2012.9

  An efficient asymmetric oxidation of prochiral sulfides catalyzed by a series of simple in situ generated complexes based on chiral amino alcohol derived Schiff bases with Ti(Oi-Pr)(4) was carried out in presence of cheap and environmentally benign oxidant H2O2 at 0 degrees C. Prochiral sulfides were converted to respective chiral sulfoxides efficiently (conversion, 93%; up to ee, 98%) with this system in 10 h at 0 degrees C. The present study demonstrated a significant role of steric influence of the substituent attached on both aryl and alkyl moiety on the enantioselectivity. Kinetic studies of the catalytic reaction showed first order dependence on substrate and catalyst whereas it is zero for the oxidant. Kinetic studies in combination with UV-vis. spectral studies were used to propose a catalytic cycle for the sulfoxidation reaction. (c) 2012 Elsevier B.V. All rights reserved.